Heterocyclization and functionalization of 1,2-bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl)benzene

1,2-Bis(4-amino-5-mercapto-1,2,4-triazol-3-yl)benzene (3) was synthesized from the reaction of phthalic acid with thiocarbohydrazide. Reaction of 3 with ethylbromoactate or ethylchloroacetate afforded compound 4. Heating of 3 with chloroacetyl chloride or chloroacetic acid gave triazolothiadiazinone 5 and 8, respectively. Refluxing of 3 with phenacyl bromide resulted in benzoylmethylthiotriazole 9. Treatment of 3 with chloroacetamide or benzyl chloride yielded 11 and 13, respectively. Condensation of 3 with benzaldehyde or m-nitrobenzaldehyde gave the products 14a and 14b in the ratio 1:2, and 15, respectively.